Gender inequality in education has been well documented in the literature, in light of family and school socialization. We build on this literature and focus from a micro sociological perspective on the emergence of 'critical reflexivity' in the specific case of a group of university scholarship students in Lebanon. Through observations and in-depth interviews, we identify gender differentiated prior dispositions that influence university experiences of those students and their career plans and demonstrate that critical reflexivity involves a process of negotiation between two fields. Family control was associated with success in studies at the expense of the social aspects of university. Gendered norms also reflected on their choices of major. Furthermore, in examining cases of emergence of reflexivity, we find that prior socialization experiences, namely degree of social conservatism, experience of change as well as social heterogeneity, influence the development of 'critical reflexivity' as students encountered a new social environment.